AU1374399A - Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts - Google Patents
Schiff base derivatives of ruthenium and osmium olefin metathesis catalystsInfo
- Publication number
- AU1374399A AU1374399A AU13743/99A AU1374399A AU1374399A AU 1374399 A AU1374399 A AU 1374399A AU 13743/99 A AU13743/99 A AU 13743/99A AU 1374399 A AU1374399 A AU 1374399A AU 1374399 A AU1374399 A AU 1374399A
- Authority
- AU
- Australia
- Prior art keywords
- catalysts
- ruthenium
- schiff base
- base derivatives
- metathesis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title abstract 9
- 239000002262 Schiff base Substances 0.000 title abstract 4
- 229910052762 osmium Inorganic materials 0.000 title abstract 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 title abstract 4
- -1 Schiff base derivatives of ruthenium Chemical class 0.000 title abstract 2
- 238000005865 alkene metathesis reaction Methods 0.000 title abstract 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 2
- 150000004753 Schiff bases Chemical class 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 238000005649 metathesis reaction Methods 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- 229910052707 ruthenium Inorganic materials 0.000 abstract 2
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003586 protic polar solvent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The present invention generally relates to ruthenium and osmium carbene catalysts for use in olefin metathesis reactions. More particularly, the present invention relates to Schiff base derivatives of ruthenium and osmium carbene catalysts and methods for making the same. The inventive catalysts are generally prepared by the treatment of unmodified catalysts with the salts of the desired Schiff base ligands, in which an anionic and a neutral electron donating ligands of the unmodified catalysts are simultaneously replaced. The Schiff base derivatives of the ruthenium and osmium carbene catalysts show unexpectedly improved thermal stability while maintaining high metathesis activity, even in polar protic solvents. Although the inventive catalysts may be used in all metathesis reactions, use of these catalysts for ring-closing metathesis ("RCM") reactions is particularly preferred.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6672197P | 1997-11-21 | 1997-11-21 | |
US60066721 | 1997-11-21 | ||
US09192175 | 1998-11-12 | ||
US09/192,175 US5977393A (en) | 1997-11-21 | 1998-11-12 | Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts |
PCT/US1998/023259 WO1999026949A1 (en) | 1997-11-21 | 1998-11-19 | Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts |
Publications (1)
Publication Number | Publication Date |
---|---|
AU1374399A true AU1374399A (en) | 1999-06-15 |
Family
ID=26747086
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU13743/99A Abandoned AU1374399A (en) | 1997-11-21 | 1998-11-19 | Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts |
Country Status (8)
Country | Link |
---|---|
US (1) | US5977393A (en) |
EP (1) | EP1042333B1 (en) |
JP (1) | JP4409087B2 (en) |
AT (1) | ATE268334T1 (en) |
AU (1) | AU1374399A (en) |
DE (1) | DE69824314T2 (en) |
ES (1) | ES2222616T3 (en) |
WO (1) | WO1999026949A1 (en) |
Families Citing this family (63)
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---|---|---|---|---|
US6156692A (en) * | 1996-04-30 | 2000-12-05 | Bp Amoco Corporation | Ruthenium-containing catalyst composition for olefin metathesis |
US6159890A (en) * | 1996-04-30 | 2000-12-12 | Bp Amoco Corporation | Ruthenium-containing catalyst system for olefin metathesis |
EP0844263B1 (en) * | 1996-11-15 | 2003-01-15 | Ciba SC Holding AG | Catalytic mixture for ring-opening metathesis polymerization |
EP0971941B1 (en) * | 1997-03-06 | 2003-09-17 | Ciba SC Holding AG | New catalysts |
US6410664B1 (en) | 1997-03-24 | 2002-06-25 | Cryovac, Inc. | Catalyst compositions and processes for olefin polymers and copolymers |
US6294495B1 (en) * | 1998-05-01 | 2001-09-25 | Exxonmobil Chemicals Patent Inc. | Tridentate ligand-containing metal catalyst complexes for olefin polymerization |
US6900347B2 (en) | 1998-09-01 | 2005-05-31 | Tilliechem, Inc. | Impurity inhibition in olefin metathesis reactions |
US7507854B2 (en) * | 1998-09-01 | 2009-03-24 | Materia, Inc. | Impurity reduction in Olefin metathesis reactions |
US6696597B2 (en) | 1998-09-01 | 2004-02-24 | Tilliechem, Inc. | Metathesis syntheses of pheromones or their components |
EP1115491B1 (en) | 1998-09-10 | 2009-08-05 | University Of New Orleans Foundation | Catalyst complex with phenylindenylidene ligand |
EP1161460B1 (en) * | 1999-02-05 | 2005-08-31 | Advanced Polymer Technologies, Inc. | Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use |
AU2002221605A1 (en) * | 2000-09-19 | 2002-04-02 | Basf Aktiengesellschaft | Dicationic ruthenium complexes and use of the same for olefin metathesis reactions |
DE10137051A1 (en) * | 2001-07-31 | 2003-02-20 | Bayer Ag | New transition metal complexes with 2-alkoxybenzylidene ligands and hydrogenated imidazole ligands, useful as catalysts in metathesis reactions |
EP1446284B1 (en) * | 2001-08-30 | 2008-10-01 | Materia, Inc. | Infusion of cyclic olefin resins into porous materials |
EP1455937B1 (en) * | 2001-11-15 | 2018-04-11 | Materia, Inc. | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
EP1329455A1 (en) * | 2002-01-22 | 2003-07-23 | Universiteit Gent | Metal carbene complexes, methods and intermediates for making them and their use in metathesis reactions |
DE60327378D1 (en) | 2002-01-22 | 2009-06-04 | Telene S A S | Metal complexes for metathesis, atom transfer radical reactions. Addition polymerization and vinylation reactions, processes and intermediates for their preparation. |
US7005525B2 (en) * | 2002-12-17 | 2006-02-28 | Brookhaven Science Associates, Llc | Recyclable catalysts methods of making and using the same |
US6737531B1 (en) | 2002-12-17 | 2004-05-18 | Brookhaven Science Associates, Llc | Catalysts for hydrogenation and hydrosilylation, methods of making and using the same |
BRPI0406756A (en) * | 2003-01-13 | 2005-12-20 | Cargill Inc | Method for the manufacture of industrial chemical agents |
EP1855861A4 (en) * | 2003-07-18 | 2010-12-01 | Univ Northwestern | Surface and site-specific polymerization by direct-write lithography |
CA2535584A1 (en) | 2003-08-13 | 2005-02-24 | University Of South Florida | Platinum complexes for the treatment of tumors |
US20070185343A1 (en) * | 2004-02-26 | 2007-08-09 | Universiteit Gent | Metal complexes for use in olefin metathesis and atom group transfer reactions |
CN1926081B (en) | 2004-02-26 | 2011-06-15 | 特林公司 | Metal complexes for use in olefin methathesis and atom or group transfer reactions |
GB0517137D0 (en) * | 2005-08-22 | 2005-09-28 | Viacatt N V | Multicoordinated metal complexes for use in metalthesis reactions |
WO2007081987A2 (en) * | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
EP2046719B1 (en) | 2006-07-12 | 2013-09-04 | Elevance Renewable Sciences, Inc. | Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like |
US8067610B2 (en) | 2006-07-13 | 2011-11-29 | Yann Schrodi | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
WO2008027267A2 (en) * | 2006-08-25 | 2008-03-06 | Dow Global Technologies Inc. | Production of random blockcopolymers via high melting polymer segment metathesis |
CA2661749C (en) | 2006-08-25 | 2014-09-16 | Dow Global Technologies Inc. | Production of telechelic compounds by metathesis depolymerization |
EP2057205B1 (en) | 2006-08-25 | 2017-02-08 | Dow Global Technologies LLC | Production of meta-block copolymers by polymer segment interchange |
US8048961B2 (en) * | 2006-08-25 | 2011-11-01 | Dow Global Technologies Llc | Production of metathesis products by amorphous polymer segment interchange |
EP3281931A1 (en) | 2006-10-13 | 2018-02-14 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis |
WO2008048520A2 (en) | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
US8501973B2 (en) * | 2006-10-13 | 2013-08-06 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
US20080306230A1 (en) * | 2007-06-07 | 2008-12-11 | General Electric Company | Composition and Associated Method |
EP2170914A1 (en) * | 2007-06-20 | 2010-04-07 | Agency for Science, Technology and Research | N-heterocyclic carbene metallacycle catalysts and methods |
US8241575B2 (en) * | 2008-01-28 | 2012-08-14 | The Johns Hopkins University | Molecularly imprinted polymer sensor device |
JP5563748B2 (en) * | 2008-04-24 | 2014-07-30 | Rimtec株式会社 | Reaction stock solution for reaction injection molding, reaction injection molding method and reaction injection molded body |
EP2280017B1 (en) * | 2009-07-21 | 2013-01-02 | Rimtec Corporation | Catalytic complex for olefin metathesis reactions, process for the preparation thereof and use thereof |
AU2011293852B2 (en) | 2010-08-23 | 2016-05-26 | Materia, Inc. | VARTM flow modifications for low viscosity resin systems |
JP6141268B2 (en) | 2011-06-17 | 2017-06-07 | マテリア, インコーポレイテッド | Adhesion promoter and gel modifier for olefin metathesis compositions |
MX352266B (en) * | 2011-09-14 | 2017-11-16 | Materia Inc | Improved electrolytic cell covers comprising a resin composition polymerized with a group 8 olefin metathesis catalyst. |
WO2013082264A1 (en) | 2011-12-02 | 2013-06-06 | Amyris, Inc. | Synthesis of olefins |
WO2014022482A1 (en) | 2012-08-01 | 2014-02-06 | California Institute Of Technology | Solvent-free enyne metathesis polymerization |
US9234985B2 (en) | 2012-08-01 | 2016-01-12 | California Institute Of Technology | Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization |
WO2014055720A1 (en) | 2012-10-05 | 2014-04-10 | California Institute Of Technology | Photoinitiated olefin metathesis polymerization |
US9527982B2 (en) | 2012-12-19 | 2016-12-27 | Materia, Inc. | Storage stable adhesion promoter compositions for cyclic olefin resin compositions |
US9598531B2 (en) | 2013-02-27 | 2017-03-21 | Materia, Inc. | Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts |
WO2014134333A1 (en) | 2013-02-27 | 2014-09-04 | Materia, Inc. | Metal carbene olefin metathesis two catalyst composition |
WO2014144634A1 (en) | 2013-03-15 | 2014-09-18 | Materia, Inc. | In-mold coating of romp polymers |
BR112015025850B1 (en) | 2013-04-09 | 2021-11-03 | Materia, Inc | METHOD TO PRODUCE AT LEAST ONE CROSS METATHESIS PRODUCT |
WO2014198022A1 (en) * | 2013-06-09 | 2014-12-18 | Lanxess Deutschland Gmbh | Ruthenium- or osmium-based complex catalysts |
MX2015017461A (en) | 2013-06-24 | 2016-08-12 | Materia Inc | Thermal insulation. |
EP3016991B1 (en) | 2013-07-03 | 2024-06-12 | Materia, Inc. | Liquid molding compositions |
EP3041812B1 (en) | 2013-09-04 | 2022-08-10 | California Institute of Technology | Functionalized linear and cyclic polyolefins |
WO2015065649A1 (en) | 2013-10-30 | 2015-05-07 | California Institute Of Technology | Direct photopatterning of robust and diverse materials |
CA2940338C (en) | 2014-02-27 | 2023-02-21 | Materia, Inc. | Adhesion promoter compositions for cyclic olefin resin compositions |
US10160828B2 (en) | 2014-07-03 | 2018-12-25 | Guang Ming Innovation Company (Wuhan) | Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction |
EP3256505B1 (en) | 2015-02-12 | 2023-11-29 | Materia, Inc. | Cyclic olefin resin compositions comprising functional elastomers |
CN107250202B (en) | 2015-02-14 | 2021-10-01 | 马特里亚公司 | ROMP polymers with improved resistance to hydrocarbon fluids |
EP3515885B1 (en) | 2016-09-23 | 2023-12-13 | Umicore Ag & Co. Kg | Preparation of amino acids and amino acid derivatives |
US11713361B2 (en) | 2018-04-20 | 2023-08-01 | Arlanxeo Deutschland Gmbh | Hydrogenation catalyst compositions and their use for hydrogenation of nitrile rubber |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5710298A (en) * | 1992-04-03 | 1998-01-20 | California Institute Of Technology | Method of preparing ruthenium and osmium carbene complexes |
US5312940A (en) * | 1992-04-03 | 1994-05-17 | California Institute Of Technology | Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization |
US5840820A (en) * | 1995-04-13 | 1998-11-24 | The University Of North Carolina At Chapel Hill | Olefin metathesis reactions in carbon dioxide medium |
US5831108A (en) * | 1995-08-03 | 1998-11-03 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
-
1998
- 1998-11-12 US US09/192,175 patent/US5977393A/en not_active Expired - Lifetime
- 1998-11-19 EP EP98957497A patent/EP1042333B1/en not_active Expired - Lifetime
- 1998-11-19 ES ES98957497T patent/ES2222616T3/en not_active Expired - Lifetime
- 1998-11-19 AT AT98957497T patent/ATE268334T1/en not_active IP Right Cessation
- 1998-11-19 JP JP2000522106A patent/JP4409087B2/en not_active Expired - Fee Related
- 1998-11-19 WO PCT/US1998/023259 patent/WO1999026949A1/en active IP Right Grant
- 1998-11-19 DE DE69824314T patent/DE69824314T2/en not_active Expired - Lifetime
- 1998-11-19 AU AU13743/99A patent/AU1374399A/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ATE268334T1 (en) | 2004-06-15 |
EP1042333A1 (en) | 2000-10-11 |
ES2222616T3 (en) | 2005-02-01 |
JP4409087B2 (en) | 2010-02-03 |
EP1042333B1 (en) | 2004-06-02 |
WO1999026949A1 (en) | 1999-06-03 |
JP2002503640A (en) | 2002-02-05 |
DE69824314D1 (en) | 2004-07-08 |
EP1042333A4 (en) | 2002-05-02 |
US5977393A (en) | 1999-11-02 |
DE69824314T2 (en) | 2005-06-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK6 | Application lapsed section 142(2)(f)/reg. 8.3(3) - pct applic. not entering national phase |